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The 16 Best Things to Do in Woodstock, Vermont

Located in Windsor County, Woodstock, Vermont, is considered one of the most beautiful small towns in the United States. With this in mind, we think it’s a must-see stop on any New England road trip.

Especially in the fall, Woodstock is full of leaf peepers from nearby states, such as Massachusetts, New York, New Jersey, Connecticut, and New Hampshire. To help you make the most of your visit, we’ll review the 16 best things to do in Woodstock, Vermont, including top activities, nearby hiking trails, and places to take pictures.

Plus, we’ll reveal the best places to eat and where to stay in Woodstock so you can plan the best vacation possible. Please note that we’ve also included a few things to do in Quechee in this list since it’s such a short distance away!

Disclaimer: This article contains affiliate links. I may earn a small commission when you book an activity or reservation through these links at no extra cost to you.

The best things to do in Woodstock (& Quechee!)

Historic homes in Woodstock, VT along Pleasant Street decorated for fall.

Historic homes along Pleasant Street in Woodstock, Vermont.

Visit Marsh-Billings-Rockefeller National Historical Park.

You can find some of the best outdoor activities in Woodstock at Marsh-Billings-Rockefeller National Historical Park, featuring over 20 miles of trails and carriage roads. The property’s name refers to its many famous owners: George Perkins Marsh, Mary Montagu Billings French, Laurance Rockefeller, and Mary French Rockefeller.

Interestingly, it’s the only national park in the state of Vermont! Some of the most popular hikes here include the Faulkner Trail, which leads to a sweeping view of Woodstock, or the Pogue and Mount Tom Trail

The Marsh-Billings-Rockefeller Mansion offers guided tours from late May through the end of October. Since tours are limited, we highly recommend making a reservation in advance. Note that parking is shared with the Billings Farm Museum.

Experience a fully operating dairy farm at Billings Farm & Museum.

View of Billings Farm & Museum in the fall.

View of Billings Farm & Museum in Woodstock, VT the fall.

Just down the road from the Woodstock Village Historic District, you’ll come across Billings Farm & Museum. This outdoor history museum serves as an operating dairy farm and a gateway to Vermont’s rural past.

Especially if you’re traveling to Vermont with kids, Billings Farm & Museum is a must-do activity in Woodstock. Plan to spend at least two hours here to experience the interactive programs, including events like milking and cheesemaking demonstrations.

Another big plus is that petting the animals is encouraged! Afterward, don’t miss the Farmhouse Scoop Shop and Gift Shop, located next to the 1890 Farm Manager’s House.

Here, you can sample Vermont-made ice cream, Billings Farm cheddar cheeses, and maybe even a fresh cider donut (available in the fall)! For more information about the cost of admission and operating hours for Billings Farm & Museum, click here

Explore downtown Woodstock on foot.

Historic Ebenezer Fitch House in Woodstock, Vermont in the fall.

The Historic Ebenezer Fitch House on The Green in Woodstock, VT.

One of the best activities in Woodstock is to take your time to walk around and fully experience the town. We suggest parking near the central square, called the Green. Then, make your way down the main road, Central Street, and later cross onto Elm Street, towards the Ottauquechee River.

Strolling through this village in New England in the fall truly feels like taking a step back in time! On your walk, check out some of the town’s highlights: the 1883 Norman Williams Public Library and the historic hotel Woodstock Inn.

For golf lovers, you’ll also find the Woodstock Country Club here, home to one of the best golf courses in the state. Moreover, don’t miss one of the most famous Vermont covered bridges– Middle Covered Bridge–located a short walk away. 

An extraordinary time of year to visit Woodstock is during October when you’ll see the homes surrounded by fall foliage, pumpkins, and Halloween decorations! Furthermore, Christmas is a popular season to experience the town covered in festive lights, wreaths, and other adornments.

Shop ’til you drop in Woodstock Village.

Don’t forget to pick up some souvenirs on your trip to Woodstock! One of the top things to do in town is undoubtedly to shop at the many boutiques and mom-and-pop stores. To help plan your shopping excursion, here are five local businesses to visit while you’re in Woodstock:

  • The Yankee Bookshop opened in 1935, making it the longest-running independent bookstore in Vermont. Here, you’ll find a wide selection of books, gifts, cards, vinyl records, and stationery in a cozy environment.
  • Clover Gift Shop features carefully curated gifts, home decor, and CBD products. This shop was founded in 1928 and has since become the go-to place to find unique Vermont souvenirs. For example, discover handmade mugs and jewelry, locally-produced maple syrup, and other Vermont-made gifts.
  • F.H. Gillingham & Son’s has been a Woodstock institution since 1886. Nowadays, this general store is best known for its high-quality Vermont products, such as maple syrup, cheeses, sweets, clothing, and gifts.
  • The Vermont Flannel Company sells an important Vermonter staple: soft and warm flannel made in the USA! You can find everything from flannel shirts and pajamas to flannel blankets in this store.
  • Danforth Pewter opened in Woodstock over 40 years ago and sells handcrafted pewter gifts made in Vermont. Some of their most coveted products include one-of-a-kind oil lamps, ornaments, jewelry, vases, and picture frames.

Admire the covered bridges around town.

Middle Covered Bridge in downtown Woodstock, VT.

Middle Covered Bridge in the fall in downtown Woodstock.

Did you know that the state of Vermont is famous for its high concentration of historic covered bridges? While in the Woodstock area, there are four main covered bridges nearby: Middle Covered Bridge, Taftsville Covered Bridge, Lincoln Covered Bridge (West Woodstock), and Quechee Covered Bridge.

If you only have time to visit one, we recommend walking by Middle Covered Bridge as you explore Woodstock Village. This 139-foot-long bridge was built in 1969 to replace an old iron bridge and sits next to The Green. Furthermore, it’s one of the most popular Instagram spots in Woodstock!

Read More: The 14 Best Things to Do in Stowe, Vermont

Try Vermont maple syrup and cheese at Sugarbush Farm.

Sugarbush Farm sits just five miles outside the town of Woodstock and is the perfect place to visit with the whole family. Kids love seeing the farm animals, the drive up to the farm is absolutely stunning, and admission is free!

Plus, you can pick up local souvenirs here, such as Vermont maple syrup made on the farm and cheeses. In fact, this family-owned farm produces 15 kinds of waxed cheese and four grades of pure maple syrup.

As you explore the property, you’ll learn all about the syrup-making process, beginning with tree tapping. Moreover, you’ll get to sample syrup and cheese on your visit before passing through the gift shop. Before you head out, don’t miss the short nature trail behind the parking lot! 

Sample homemade ice cream.

Mountain Creamery serves the best dessert in Woodstock: homemade ice cream. If you want to try a unique flavor, order the Vermont Maple Walnut, which includes real Vermont maple syrup!

Additionally, make sure to sample their seasonal flavor–it’s pumpkin ice cream in the fall. You can find a current list of flavors here. If you’re not a big fan of ice cream, Mountain Creamery also serves fresh pastries that are made daily on the premises.

The most famous is undoubtedly the Mile-High Apple Pie, which can be served with vanilla ice cream or Vermont cheddar. Note that this creamery is cash only and is closed on Wednesdays.

Shop local at Woodstock Farmers’ Market.

The Woodstock Farmers’ Market is open year-round, serving the community delicious local food in two locations: Woodstock and Waterbury, Vermont. This gourmet grocery store offers fresh organic produce, grab-and-go sandwiches, coffee and espresso, baked goods, meats and cheeses, and other Vermont-made food items.

Plus, the Woodstock location sits a convenient three minutes from the historic village (by car). On your visit, we suggest picking up sandwiches as a quick and easy lunch–the Moonlight in Vermont is a customer favorite! If you’d like to see all the options for to-go food, you can read the full grab-n-go menu here.

Additionally, the Farmers’ Market makes a great stop on a Vermont road trip to rest and recharge with coffee and freshly baked pastries. Before you stop by, remember that the market is closed on Sundays and Mondays! Its current hours are from 8 a.m.-6 p.m., Tuesdays through Saturdays.

If you have extra time and are on the hunt for more Vermont products, we suggest a short drive to the South Woodstock Country Store. Here, you can find locally sourced food and other goods, like cheese, beer, and snacks.

Handle a falcon with New England Falconry.

For wildlife enthusiasts visiting Woodstock, Vermont, New England Falconry is an absolute must-do activity. This unique experience is made possible through a partnership with the Woodstock Inn and Resort and is led by Master Falconer Chris Davis.

At New England Falconry, you’ll delve into the captivating world of these majestic creatures, gaining insight into their remarkable adaptations, the imperative need for their conservation, and the fascinating history of falconry. However, the highlight of this encounter lies in the opportunity to handle and fly trained falcons! 

Whether you opt for the introductory session, extended session, owl experience, or the comprehensive eagle session, each offers a unique perspective on these magnificent birds and their place in the natural world. Appointments are necessary for all sessions, and participants must be at least 8 years old.

Take a photo at the instagrammable Sleepy Hollow Farm.

View of Sleepy Hollow Farm with fall foliage in Pomfret, VT.

Sleepy Hollow Farm in Pomfret, Vermont, during the fall season.

If you’re planning to travel to Vermont in the fall, you’ve most likely seen photos of Sleepy Hollow Farm. In fact, it’s likely one of the most photographed properties in the state!

Sleepy Hollow is a short eight-minute from Woodstock Village, down Cloudland Road in Pomfret. Recently, this farm has exploded on Instagram, making it one of the best places to visit in Woodstock for photos. 

Therefore, we suggest visiting early in the morning for the best lighting with the least crowds (especially on weekends). As you may have guessed, the most popular time for visitors to photograph Sleepy Hollow is at sunset. If you choose to visit, please remember that this location is private property.

Security gates and cameras are set up for a reason, so please do NOT trespass while taking your pictures. If you’re looking for another similar photo opportunity, you don’t want to miss Jenne Road Farm, which is about a 20-minute drive away.

Regrettably, this year, the residents of Pomfret village have chosen to temporarily block access to the main road near Sleepy Hollow Farm, spanning from September 23 to October 15. The rationale behind this petition stems from the residents’ irritation with the constant stream of tourists who come in search of picturesque autumn views.

Taste local beer.

You can’t visit Vermont without tasting some of the state’s famous craft beers! With this in mind, we highly recommend taking a short 15-minute drive to Bridgewater, where you can find Long Trail Brewing Co.

This German-inspired brewery gets its name from a popular hiking trail that runs through Vermont and is a must-visit for any beer lover. It offers more than a dozen beers on tap, including the flagship Long Trail Ale and various specialty IPAs.

Even if you’re not into beer, Long Trail has something for everyone: hard cider, wines, CBD seltzers, and delicious bar snacks made with locally-sourced ingredients. Not to mention, the brewery also has an incredible view of the Ottauqueechee River out back.

Hike the Quechee Gorge Trail.

View of Quechee Gorge from Route 4 Bridge

View of Quechee Gorge from the Route 4 bridge in Quechee, VT.

If you’re looking for hiking near the city of Woodstock, we highly recommend checking out the Quechee Gorge Trail. This 2.7-mile easy trek is within Quechee State Park and features beautiful views of the Ottauquechee River and Quechee Gorge.

In case you didn’t know, many people call this gorge “Vermont’s Little Grand Canyon”! If you’d like to make the hike a little shorter, you can park at the visitor center and begin the walk to the bottom of Quechee Gorge from there.

There’s usually plenty of parking at this location, making it an easy outdoor activity to do on your visit this Vermont city. Additionally, you can find an official trail guide here for more information. 

Pro tip: Make sure to walk over the Quechee Gorge Bridge (on Route 4). This spot is one of the best places to take pictures of Quechee Gorge!

Watch a glassblowing demonstration.

While you’re in the Woodstock area, you won’t want to pass up the opportunity to visit the Simon Pearce flagship store in Quechee. Pearce is famous globally for his glassblowing and pottery work, thanks to the skill and dedication poured into every individual item.

So, you won’t want to miss the chance to watch artisans implement his techniques in the glassblowing studio here! You can catch live glassblowing demonstrations Friday through Monday from 10 a.m. to 2 p.m. or Tuesday through Thursday from 10 a.m. to 4 p.m..

Apart from the glassblowing expos, this location also serves as a showroom, a shop, and even has a restaurant. The store features glass and pottery designs that make amazing souvenirs, along with a selection of curated home accents.

Meanwhile, the farm-to-table restaurant was chosen as one of “America’s Most Romantic Restaurants” by Travel and Leisure. Reservations are required for both lunch and dinner.  If you can, make sure to request a table with a view of the Ottauquechee River waterfall and covered bridge! The restaurant is open Wednesday-Sunday.

Stroll the forest canopy walk at VINS Nature Center.

The Vermont Institute of Natural Science, based in Quechee, Vermont, seeks to serve the community through educating others, researching, and providing avian wildlife rehabilitation. On your visit, you can explore outdoor exhibits featuring raptor enclosures, a songbird aviary, an adventure playscape, and nature trails.

Additionally, VINS recently opened a Forest Canopy Walk! This boardwalk experience allows visitors to view the forest and the Ottauquechee River from the Center without actually having to make the climb. Therefore, it’s an ideal activity for the whole family, including grandparents and kids.

If you’re visiting with kids, you won’t want to miss the daily live bird programs, including Predators of the Sky and Raptors Up Close. For a complete list of daily events, click here. VINS Nature Center is open every day from 10 a.m. to 5 p.m., and tickets are $19 for adults, $16 for children between 4-17, and free for children three and younger.

Go antiquing at the Vermont Antique Mall in Quechee.

The Vermont Antique Mall in Quechee, VT.

The Vermont Antique Mall in Quechee, VT.

If you’re wondering what to do in Woodstock on a rainy day, we suggest stopping by the Vermont Antique Mall! This shopping center, situated in a 17,000 sq foot barn in Quechee Gorge Village, is open daily from 10 a.m. to 5 p.m.

The mall itself is actually a collection of different stores, including a souvenir shop, a Cabot cheese store, a toy museum, and antique shops. As you peruse the antique section, you’ll come across various collectibles and items for the home, including books, furniture, cast iron skillets, pots, and other knick-knacks.

Go skiing at Saskadena Six.

If you’re visiting Woodstock during the winter months, you won’t want to miss the chance to go skiing at one of the oldest ski areas in the United States. Formerly known as “Suicide Six”, the newly renamed Saskadena Six is home to 24 trails and slopes.

Plus, it’s located in Pomfret–only a seven-minute drive from The Green in Woodstock Village. Saskadena Six also offers a variety of outdoor activities in the summertime. For example, you can enjoy mountain biking, fly fishing, or hiking during the warmer months.

Where to eat in Woodstock, VT

The Prince & The Pauper Restaurant in Woodstock Village, Vermont.

The Prince & The Pauper Restaurant in Woodstock Village.

Woodstock, Vermont, has a diverse array of places to eat and experience local food. If you’re having trouble deciding where to dine, here are some of our favorite establishments in town and nearby:

  • Mon Vert Cafe is an organic cafe serving breakfast and lunch fare, artisanal coffee, and pastries. Many Woodstock visitors consider this spot to have the best breakfast in town. Quick note: Mon Vert Cafe does not take reservations and is very laid-back, so I wouldn’t try to stop by if you’re in a rush!
  • Cloudland Farm, located in Pomfret, is home to a restaurant where you can experience authentic farm-to-table dining. This locale currently offers indoor dining on Thursdays, Fridays, and Saturdays and requires reservations. As you can imagine, we suggest securing a reservation in advance if you’d like to visit on a particular day.
  • The Prince and the Pauper Restaurant offers an elegant dining experience in the Center of Woodstock Village. It’s open for dinner from 5–8 p.m. Tuesdays through Saturdays, and reservations are required for both table and bar seating. Regarding the menu, this restaurant serves a three-course Prix Fixe spread, which includes an appetizer, salad, and entrée.
  • Abracadabra Coffee is a pop-up coffee shop in Woodstock open Wednesday through Sunday. This Vermont specialty coffee roaster is well worth a visit, serving all your coffee favorites and seasonal signature drinks, house-made syrups, liége waffles, donuts, and canelés.

Where to stay in Woodstock, VT

The Woodstock Inn & Resort on The Green in Woodstock, VT.

The Woodstock Inn & Resort on The Green in Woodstock, VT.

In this section, we’ll discuss the best places to stay in Woodstock. Remember that Woodstock is a relatively small town. So, especially during high season, it’s important to book your accommodations as soon as possible. Here are four of our preferred local hotels, all in central locations:

  • Woodstock Inn & Resort is the most famous place to stay in town, located on The Green. This historic hotel has ties to the Rockefeller family, who purchased the original inn in 1967, renovated it, and reopened the property under the same name in 1970. If you can afford to splurge on accommodations in Woodstock, this is definitely the place to do it! During the winter season, you can even go skiing at Woodstock Inn’s Suicide Six ski hill.
  • 506 On The River Inn Woodstock is a family-owned luxury resort near Woodstock Village, offering 45 rooms and suites with river and garden views. Furthermore, the property has an indoor pool, sauna, gym, game rooms, and 506 Bistro & Bar.
  • The Village Inn of Woodstock is a charming adult-only bed and breakfast located less than a mile from the Billings Farm and Museum in Woodstock. This luxurious Vermont inn offers eight romantic guest rooms. Moreover, it has a tavern and a serene terrace with a pond and perennial garden, as well as ample free parking for guests.
  • The Shire Woodstock is an independent hotel located in the heart of the Village of Woodstock. Due to its location along the Ottauquechee River, many of the property’s 50 rooms feature a scenic view. There are also a limited number of rooms with fireplaces and jacuzzis! Moreover, The Shire offers the option to book a dog-friendly suite.

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Woodstock, Vermont is the perfect destination for a getaway no matter the time of year. Nestled in the Green Mountains, this quaint town is the perfect place to relax and enjoy the outdoors. There are hiking trails for all skill levels, photo spots around every corner, and plenty of chances to explore the local history and culture. Here's your ultimate guide to things to do and where to stay in Woodstock, Vermont.

This article was first published in October 2021 and has since been updated.

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